Hydrochloric Acid → Hydrochloric Acid

HRID 527752Notes

Reaction equation

HRID 527752 reaction equation
C(OC([NH:8][C@H:9]([C:29]([N:31]1[C@H:35]([C:36](=[O:48])[NH:37][C@H:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][CH2:40][CH2:39]2)[CH2:34][Si:33]([CH3:50])([CH3:49])[CH2:32]1)=[O:30])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.[ClH:51]>C(Cl)Cl>[NH2:8][C@H:9]([C:29]([N:31]1[C@H:35]([C:36](=[O:48])[NH:37][C@H:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][CH2:40][CH2:39]2)[CH2:34][Si:33]([CH3:50])([CH3:49])[CH2:32]1)=[O:30])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)=[CH:13][CH:12]=1.[ClH:51]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131735603HCID 131735603, compound

Product 2

HCID 313Hydrochloric AcidYield 1,687.8%HCID 89930881HCID 89930881, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-((4-((S)-2-((tert-butoxycarbonyl)amino)-3-((R)-3,3-dimethyl-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,3-azasilolidin-1-yl)-3-oxopropyl)phenyl)ethynyl)benzoate (92 mg, 0.13 mmol) in DCM (2 mL) was added HCl (4.0 M solution in dioxane, 0.5 mL, 2.00 mmol). The reaction mixture was stirred at rt for 4 h and concentrated in vacuo to give the title compound as a HCl salt (80 mg, 95%, brown solid). MS(ESI+) m/z 594.5 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-380aac4c182144019379dd1dd2b4024d
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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